Cinnamon Sugar Vanilla Bean Challah with Whiskey Soaked Golden Raisins

I’ve been thinking about the future a lot lately.

Do you do this…? Daydream about the days to come?

I do my best not to. I try to be in the here. I strive to stay in the now. But sometimes my brain gets the best of me and dives deep into a mental Q & A.

The questions internally pondered border on irrelevant to life changing: How long will I stay in New York? What am I really doing with my life? Paris? Is he… the one? What should I pack on my trip to California this April? Do I really need those cute salt and pepper shakers from anthro…(the answer to that one is yes.).

Questions, questions, questions! Indulging the mind is a slippery slope.

Baking this bread last weekend was exactly what I needed to bring me back from the Land of No Answers and into the exact moment I was living – which is indeed the very best place to be. The process forced me to concentrate on the here and now. Kneading the sticky dough gently eased my mind away from life’s big questions, and guided it to the reality of it all: life is like totally awesome right now, silly.

This challah is slightly time consuming (most of it’s waiting for the dough to raise, so you’re free to do your thing during that time), and it does take a wee bit of concentration (have you ever braided a challah!? Pay attention), but it’s 100% worth your labor and efforts.

With streaks of cinnamon-sugar, speckles of vanilla bean, and even a few drunken raisins, this is one bread that will 100% have you challah back. Challah! 

Cinnamon Sugar Vanilla Bean Challah with Whiskey Soaked Golden Raisins – Yields 2 loaves 

Adapted from Joan Nathan via Smitten Kitchen 

Time: about 1 hour, plus 2 1/2 hours’ rising

1 1/2 packages active dry yeast (1 1/2 tablespoons or 3/8 ounces or 11 grams)

1 tablespoon (13 grams) plus 1/2 cup (100 grams) sugar

1/2 cup olive oil

5 large eggs, at room temperature

1 tablespoon salt

1 teaspoon cinnamon

8 1/2- 9 cups all-purpose flour

2 vanilla beans, scraped

4 oz whiskey – I used crown royal, but I’m sure whatever you have on hand (if you keep whiskey on hand) will work fine.

1/2 cup golden raisins per challah, soaked in the whiskey for at least 3 hours, preferably overnight.

1/2 cup granulated sugar mixed with 2 tablespoons cinnamon

In a large bowl, dissolve the yeast and 1 tablespoon of the sugar in 1 3/4 cups lukewarm water.

Whisk the olive oil into the yeast, then beat in 4 eggs, one at a time, with remaining sugar, salt, cinnamon, and vanilla beans. Gradually add flour. When the dough holds together, (I used the full 9 cups) it is ready for kneading. I did this all by hand, but you could use your mixer if the bowl is big enough; mine was not.

Turn the dough onto a floured surface and knead until smooth. Clean out the bowl and grease it, then return the dough to the bowl. Cover with plastic wrap, and let the dough rise in a warm place for 1 hour, until almost doubled in size. Dough may also rise in an oven that has been warmed to 150 degrees then turned off. Punch down the dough, cover and let it rise again in a warm place for another half-hour.

At this point, you’re going to knead your whiskey soaked raisins into the challah.

Now it’s time to braid! Take half the dough and form it into 6 balls. Roll each all in the cinnamon sugar mix so it’s well coated, then, with your hands, roll each ball into a strand about 12 inches long and 1 1/2 inches wide. You can sprinkle some more cinnamon sugar on them at this point if you want – I did. Place the 6 in a row, parallel to one another. Pinch the tops of the strands together. Move the outside right strand over 2 strands. Then take the second strand from the left and move it to the far right. Take the outside left strand and move it over 2. Move second strand from the right over to the far left. Start over with the outside right strand. Continue this until all strands are braided. For a straight loaf, tuck ends underneath. For a circular loaf, twist into a circle, pinching ends together. Make a second loaf the same way. Place braided loaves on a greased cookie sheet with at least 2 inches in between.

Beat remaining egg and brush it on loaves. Either freeze breads or let rise another hour.

If baking immediately, preheat oven to 375 degrees and brush loaves again. Sprinkle with any remaining cinnamon sugar. If freezing, remove from freezer 5 hours before baking.

Bake in middle of oven for 30 to 40 minutes, or until golden. (If you have an instant read thermometer, you can take it out when it hits an internal temperature of 190 degrees.) Cool loaves on a rack.

About bakerbynature

Hi, I'm Ashley! The baker, writer, and photographer behind this blog. Welcome.
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43 Responses to Cinnamon Sugar Vanilla Bean Challah with Whiskey Soaked Golden Raisins

  1. Baking bread is definitely my favorite form of therapy!

  2. I’ve never made a yeast bread – just not my thing – although this looks so delish I may have to give it a shot! Looks SO good. I hear you about not being able to turn your brain off but I do try to live “in the now”. A work in progress :-)

  3. Is this bread for real?! I need this stat.

  4. I’ve never made challah but this recipe seems pretty straightforward, I should try it!

  5. how beautiful. this is perfect bread for christmas!

  6. This bread is so pretty, I am imagining the smell wafting through my home now, as the bread bakes (I have a good imagination).
    P.S. You sooo need the salt and pepper shakers from Anthropologie!

  7. Wait… not everyone keeps whiskey on hand? ;)

    This sounds amazing!

  8. That is a beautiful Challah and it would make some amazing french toast!!!

  9. Of course you did. You amazing little person you. Can you come and stay with me? omg!! WE can bake together! While drinking!!

  10. Suzie says:

    I have a recipe for pretzel challah that I have been meaning to make! Your version looks wonderful! Of course you must get the salt and pepper shakers. I’m the same way :)

  11. waiting for challah dough to rise is SO worth it. My mom used to make homemade challah bread and it is worth every.single.soft.bite. Your bread looks incredible – the cinnamon sugar, the vanilla, and those plump juicy soaked raisins – this is everything, EVERYTHING I simply LOVE about cinnamon raisin bread but in challah form. You hit a home run with this! beautiful.

    • Thank you, Sally!
      I actually love waiting for bread to raise, haha. It’s like recess! You can take a shower, read a book, take a nap, and come back to some dough ready to become bread – what could be better?

  12. Clearly, I need to bake more bread! I am such a future kind of person. Staying in the NOW is a major struggle for me. If challah is the answer, I’m game!

  13. i feel like my life is a constant question and that i’m ALWAYS asking and wondering about the future. challah is my FAVORITE bread of all time and i looooove this spin on it. the whiskey soaked raisins? wow, so dangerous. i’d likely be drunk while kneading the bread haha

  14. Patty says:

    I think I’m in love with a loaf of bread, so uncomplicated;-)

  15. Oh yum! I really liked reading about your mindset right now. I’m trying to relax and live in the moment, too. Life is good. Ever heard that phrase ‘life is what happens when you’re busy making other plans?’ I think that sums things up for me. Anyway, lovely bread :)

  16. I recently made challah and it’s the best bread I’ve ever made – well, the dinner rolls I made were awesome but for bread (not rolls) I loved it and your challah is drop dead gorgeous and the flavors, Ashley! This is a total winner! Cinn-sugar and whiskey soaked raisins – yes!!

  17. baker street says:

    That is one gorgeous loaf, Ashley!

  18. Erin|The Law Student's Wife says:

    Oh how I play the question game!! I can totally relate to the way baking bread clears your head. There is something beautiful and almost therapeutic about it. Thanks for sharing this recipe. It looks fantastic!

  19. Oh my gosh!
    This looks amazing! I would love to have some for our shabbat dinner tomorrow. I will have to get over my fear of yeast and try to bake some challah soon!

  20. I am kinda sorta obsessing over everything about this loaf. Never had challah bread but if it tastes half as awesome as it looks, I know my mouth will be in one heavenly place soon enough. HOLY COW.

  21. Move to Paris…and open a bakery!!! LOL! With beautiful food like this, I’m sure you’ll manage just fine…

  22. I’m the same way, I’ve been told I need to work more and being “present” but my mind tends to make that a difficult task.
    I love this bread! I bet it also makes the most amazing french toast or bread pudding.

  23. Sissi says:

    Challah brings back wonderful childhood memories… I loved it with lots of butter. Unfortunately I have never managed to make my own challah (those I have baked were more or less failures, not to mention the shape!). Yours looks soft and slightly moist, just the way I love it. Soaking raisins in whisky sounds like an excellent idea.

  24. I daydream about being able to make bread someday–I am much more a cook than I am a baker. This is just beautiful–mail me a loaf? ;)

  25. Jayne says:

    oooh…. challah! I imagine a drizzle of dulce de leche inside would add to it’s ooey gooey ness. Though that might be a pain to braid. Grated chocolate in place of cinnamon would work, no?

  26. CCU says:

    Please sell this professionally my friend it is incredible :D

    Cheers
    Choc Chip Uru

  27. Yes! Baking (or cooking) always brings me back to the present. One of my favorite things about it. =) And this challah looks amazing – YUM!

  28. Making challah is one of my favorite things ever. When it comes out of the oven, whoever I’m with and I, we just attack it. Eat it all up. Smother it in honey. It’s awesome. Such a fun event. :) And this version with it’s cinnamon sugar?! Oh boy. Dangerous.

  29. I really wish baking will become a therapeutic activity for me one day! Right now, it’s very stressful time (worrying about the result etc). :) Your challah is so beautiful. And I love the flavors. Whiskey soaked raisins, vanilla bean, and cinnamon sugar? Sounds like all in one!

  30. Gorgeous bread, gorgeous post.

    Yours in daydreaming… xox

  31. Parsley Sage says:

    Stunning! And it sounds absolutely delicious! And its better to think about the future than to dwell on the past ;)

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